Iridium Catalyzed Aerobic α,β-Dehydrogenation of γ,δ-Unsaturated Amides and Acids: Activation of Both α- and β-C-H bonds through an Allyl-Iridium Intermediate.,Journal of the American Chemical Society

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Iridium Catalyzed Aerobic α,β-Dehydrogenation of γ,δ-Unsaturated Amides and Acids: Activation of Both α- and β-C-H bonds through an Allyl-Iridium Intermediate.
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-01-08 , DOI: 10.1021/jacs.7b11351
Zhen Wang ₁ , Zhiqi He ₁ , Linrui Zhang ₁ , Yong Huang ₁

Affiliation

Direct aerobic α,β-dehydrogenation of γ,δ-unsaturated amides and acids using a simple iridium/copper relay catalysis system is described. We developed a new strategy that overcomes the challenging issue associated with the low α-acidity of amides and acids. Instead of α-C-H metalation, this reaction proceeds by β-C-H activation, which results in enhanced α-acidity. Conjugated dienamides and dienoic acids were synthesized in excellent yield with this reaction, which uses a simple reaction protocol. Mechanistic experiments suggest a catalyst resting state mechanism in which both α-C-H and β-C-H cleavage is accelerated.

中文翻译：

铱催化的 γ,δ-不饱和酰胺和酸的有氧 α,β-脱氢：通过烯丙基铱中间体激活 α- 和 β-CH 键。

描述了使用简单的铱/铜中继催化系统对 γ,δ-不饱和酰胺和酸进行直接有氧 α,β-脱氢。我们开发了一种新策略来克服与酰胺和酸的低 α 酸度相关的挑战性问题。该反应不是 α-CH 金属化，而是通过 β-CH 活化进行，从而导致 α-酸性增强。共轭二酰胺和二烯酸通过该反应以优异的产率合成，该反应使用简单的反应方案。机理实验表明催化剂静止状态机制，其中 α-CH 和 β-CH 裂解都被加速。

更新日期：2018-01-08

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